165271-66-9

Upstream product

• 15205-57-9 tribenzyl phosphite 
• 166049-88-3 benzyl bis(chloromethyl)phosphinate 
• 683-85-2 N,N-dimethylaminodichlorophosphane 
• 100-51-6 benzyl alcohol 
• 18033-91-5 P,P'-(2-ethoxy-2-oxo-2λ⁵-phospha-propane-1,3-diyl)-bis-phosphonic acid tetraethyl ester 
• 29134-54-1 tris(benzyloxy)methane 
• 166049-80-5 dibenzyl <<(benzyloxy)(chloromethyl)phosphinoyl>methyl>phosphonate 
• 396123-62-9 bis(O,O'-dibenzyl selenophosphonomethyl) N,N-dimethylaminophosphine 
• 384375-15-9 methaneselenophosphonic acid O,O'-dibenzyl ester 
• 396123-63-0 bis(O,O'-dibenzyl selenophosphonomethyl)benzyl phosphinite 

Downstream Products

• 396123-64-1 bis(O-benzylphosphonomethyl)phosphinic acid benzyl ester 
• 165271-67-0 <<(Benzyloxy)<<(benzyloxy)hydroxyphosphoryl>methyl>phosphoryl>methyl>phosphonic acid dibenzyl ester 
• 396123-73-2 C₅₇H₅₃N₁₄O₁₄P₃ 

Relevant academic research and scientific papers

An unsymmetrical approach to the synthesis of bismethylene triphosphate analogues

(Chemical Equation Presented) A protected, unsymmetrical bismethylene triphosphate analogue was prepared by sequential Michaelis-Arbuzov reactions on ethyl bis(halomethyl)phosphinates. This species was monodeprotected at one of the terminal phosphonate gr

Synthesis of enzymatically and chemically non-hydrolyzable analogues of dinucleoside triphosphates Ap3A and Gp3G

Dinucleoside polyphosphates are ubiquitous compounds tightly involved in the regulation of a number of key biological processes. Hydrolysis-resistant analogues of Ap3A and Gp3G, two important members of that family of nucleotides, have been synthesized. P1,P2.P2,P3-Bis-methylene diadenosine and diguanosine triphosphates were prepared from O,O-dialkyl methaneselenophosphonates using an original methodology. Whereas the 2-fold addition of the methanephosphonate anion to the activated phosphorus species cannot be performed, multiple condensation of lithiated methaneselenophosphonate with electrophilic trivalent phosphorus compounds is revealed to be very effective. A one-pot condensation/esterification/oxidation sequence involving O,O-dialkyl methaneselenophosphonates provides a highly efficient route to the PCH2PCH2P backbone. This new development in selenophosphonate chemistry offers a great potential for further regioselective functionalization of polyphosphate mimics.

Selenophosphonates as building blocks for the preparation of bis-methylene analogs of triphosphates

A new route to bis-methylene analogs of triphosphate esters involving carbanion chemistry is described. Lithiated methaneselenophosphonate anion is condensed several times with chlorophosphites and phosphoramidous chlorides prior to esterification/transesterification and selenation or oxidation.

First Use of Benzyl Phosphites in the Michaelis-Arbuzov Reaction Synthesis of Mono-, Di-, and Triphosphate Analogs

Benzyl phosphites were used in the Michaelis-Arbuzov reaction.Special experimental conditions allowed preparation of a set of phosphonate analogs of mono-, di-, and triphosphate.Furthermore, regioselective mono-deprotection mades these molecules useful building blocks for the synthesis of analogs of polyphosphorylated compounds of biological interest (e.g. nucleotides), after removal of all phosphonate benzyl ester groups under very mild conditions and high yields.

Synthesis of Di- and Triphosphate Ester Analogs via a Modified Michaelis-Arbuzov Reaction

For the first time, benzyl phosphites allowed the preparation of a set of polyphosphonates from chloromethyl halides via the Michaelis-Arbuzov reaction performed under vacuum.Regioselective mono-deprotection or complete deprotection of these phosphonates provide useful building blocks for the synthesis of biological phosphate analogs.